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Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139
Graphical Abstract
Scheme 1: The polyenes 2 stabilized by terminal tert-butyl substituents.
Scheme 2: The catalytic hydrogenation of diene 3.
Figure 1: The structure of compound 4 in the crystal. Ellipsoids correspond to 30% probability levels.
Scheme 3: The catalytic hydrogenation of triene 7.
Scheme 4: Addition of bromine to model dienes.
Scheme 5: Bromine addition to diene 3 and triene 7.
Scheme 6: Bromine addition to the higher oligoenes 19–22.
Figure 2: (a) The structure of compound 24 in the crystal. Ellipsoids correspond to 50% probability levels. (...
Figure 3: The structure of compound 25 in the crystal. This was a structure of poor quality and served only t...
Scheme 7: Epoxidation of triene 7 with MCPBA and DMDO.
Scheme 8: Epoxidation of tetraene 19 with MCPBA and DMDO.
Scheme 9: Diels–Alder addition of PTAD (36) to triene 7 and tetraene 19.
Figure 4: The structure of compound 37 in the crystal. Only one of two independent molecules is shown. Ellips...
Scheme 10: Diels-Alder addition of oligoenes 20 and 21 with PTAD (36).
Scheme 11: Addition of excess PTAD (36) to hexaene 21 and heptaene 22.
Scheme 12: TCNE addition to oligoolefins: from tetraene 19 to nonaene 42.
Figure 5: The structure of compound 43 in the crystal. Only one of two independent molecules is shown. Ellips...
Scheme 13: Photochemical experiments with tetraene 19.
Figure 6: The structure of compound 52 in the crystal. Ellipsoids correspond to 50% probability levels.